Tetrahedron Letters ( IF 1.5 ) Pub Date : 2021-05-17 , DOI: 10.1016/j.tetlet.2021.153182 Rulong Jia , Xiu Wang , Jinbo Hu
Organofluorine compounds often possess unique chemical, physical and biological properties and therefore, they play important roles in pharmaceuticals, agrochemicals, and advanced materials. Notably, the introduction of CF2 motif as an oxygen surrogate could significantly improve the metabolic stability and bioavailability of the target molecules. Therefore, selective introduction of the CF2 group into organic molecules is an appealing task. It has been realized that the (phenylsulfonyl)difluoromethyl group is a versatile CF2 building block, which can be readily transformed into other useful fluorinated functionalities such as difluoromethyl (CF2H), difluoromethylene (–CF2–), and difluoromethylidene (=CF2) groups. This article overviews the recent advance of (phenylsulfonyl)difluoromethylation reactions as well as their synthetic applications in organic synthesis within the past decade. Five modes of difluoroalkylation reactions have been developed, including nucleophilic (phenylsulfonyl)difluoromethylations, electrophilic (phenylsulfonyl)difluoromethylations, radical (phenylsulfonyl)difluoromethylations, difluorocarbene reactions, and transition-metal mediated (phenylsulfonyl)difluoromethylations.
中文翻译:
二氟甲基苯砜及其衍生物合成应用的新进展
有机氟化合物通常具有独特的化学、物理和生物学特性,因此它们在药物、农用化学品和先进材料中发挥着重要作用。值得注意的是,引入 CF 2基序作为氧替代物可以显着提高目标分子的代谢稳定性和生物利用度。因此,将CF 2基团选择性地引入有机分子是一项有吸引力的任务。人们已经意识到(苯磺酰基)二氟甲基是一种通用的 CF 2结构单元,它可以很容易地转化为其他有用的氟化官能团,如二氟甲基(CF 2 H)、二氟亚甲基(-CF 2 -)和二氟亚甲基(= CF2 ) 组。本文概述了近十年来(苯磺酰基)二氟甲基化反应的最新进展及其在有机合成中的合成应用。已经开发了五种二氟烷基化反应模式,包括亲核(苯磺酰基)二氟甲基化、亲电(苯磺酰基)二氟甲基化、自由基(苯磺酰基)二氟甲基化、二氟卡宾反应和过渡金属介导的(苯磺酰基)二氟甲基化。